[1] By the late 19th century, Newburgh's cemeteries had become crowded and disturbed by urban sprawl.

The expansive St. George's Cemetery, designed with Downing influence decades earlier, succumbed to these conditions as well.

[2] Instead of searching for land within the city boundaries, the association looked south to the suburb of New Windsor-on-Hudson and purchased fifty acres [2] about a mile from Quassaick Creek.

Installed in 1897, Lewis S. Sterrit anonymously donated[3] it to the cemetery for beautification purposes.

The gates are topped with a sphere on either pillar, inscribed with the words "Woodlawn" and "Cemetery."